my first time being dressed up was with an escort. she suggested it. i had already seen her 2 times to get fucked in the ass with a strapon. she suggested a roleplay scenario. she dressed me up in really slutty lingerie, a small skirt and a tight top with some breast forms in. she in turn wore male clothing. then we pretended that i was a hooker while she was the male "john". god damn it was the best strapon sex i ever had. she fucked me so hard my ass was sore the next few days.

My first time was with an ex girlfriend who knew I was bi and liked to crossdress. It was my first time crossdressed in front of a woman and the first time I had seen a real strap on outside of porn. When we split up there was a long period until I met my wife and then things got interesting, cross dressing, strap ons and double ended dildos.

My first wife, who we discovered was bisexual led me down that path. Started with oral sex and her fingering me. Moving on to a small dildo, it made for some awesome orgasms for both of us. After our first FMF threesome with one of her girl friends opened the door to some other playing. She met a girl named Samantha, or Sam for short. She wasn't really into guys, but tolerated me after we came to the understanding that I wasn't going to do anything with her. She introduced a strap-on to my wife during one of our sessions, and was pretty hot to witness. It was a while later when my wife was sucking on me but not making me cum that she said she wanted to try something. At that point I was so hard and wanted to cum...I would have agreed to most anything. She wanted to dress me up in her clothes and put makeup on me, which she did. Then back to the sucking on me, after partially undressing me. She kept me close but not letting me cum.. She had been fingering me and moved to the small vibrator she had used before. After a bit she pulled that out and moved up to kiss me. She told me she wanted to fuck me about the same time I felt something pressing into my ass and pretty much slid right in. She was wearing that strap-on of Sam's. She then proceeded to pretty much fuck me. She hit a rhythm that made me cum so hard without having my cock touched, shooting all over my chest and stomach. She told me that when I came it made her come too...

My first wife, who we discovered was bisexual led me down that path. Started with oral sex and her fingering me. Moving on to a small dildo, it made for some awesome orgasms for both of us. After our first FMF threesome with one of her girl friends opened the door to some other playing. She met a girl named Samantha, or Sam for short. She wasn't really into guys, but tolerated me after we came to the understanding that I wasn't going to do anything with her. She introduced a strap-on to my wife during one of our sessions, and was pretty hot to witness. It was a while later when my wife was sucking on me but not making me cum that she said she wanted to try something. At that point I was so hard and wanted to cum...I would have agreed to most anything. She wanted to dress me up in her clothes and put makeup on me, which she did. Then back to the sucking on me, after partially undressing me. She kept me close but not letting me cum.. She had been fingering me and moved to the small vibrator she had used before. After a bit she pulled that out and moved up to kiss me. She told me she wanted to fuck me about the same time I felt something pressing into my ass and pretty much slid right in. She was wearing that strap-on of Sam's. She then proceeded to pretty much fuck me. She hit a rhythm that made me cum so hard without having my cock touched, shooting all over my chest and stomach. She told me that when I came it made her come too...

My first wife, who we discovered was bisexual led me down that path. Started with oral sex and her fingering me. Moving on to a small dildo, it made for some awesome orgasms for both of us. After our first FMF threesome with one of her girl friends opened the door to some other playing. She met a girl named Samantha, or Sam for short. She wasn't really into guys, but tolerated me after we came to the understanding that I wasn't going to do anything with her. She introduced a strap-on to my wife during one of our sessions, and was pretty hot to witness. It was a while later when my wife was sucking on me but not making me cum that she said she wanted to try something. At that point I was so hard and wanted to cum...I would have agreed to most anything. She wanted to dress me up in her clothes and put makeup on me, which she did. Then back to the sucking on me, after partially undressing me. She kept me close but not letting me cum.. She had been fingering me and moved to the small vibrator she had used before. After a bit she pulled that out and moved up to kiss me. She told me she wanted to fuck me about the same time I felt something pressing into my ass and pretty much slid right in. She was wearing that strap-on of Sam's. She then proceeded to pretty much fuck me. She hit a rhythm that made me cum so hard without having my cock touched, shooting all over my chest and stomach. She told me that when I came it made her come too...

My wife used to humor me and do this, but not so much anymore. This is pretty much my biggest fetish and I'd do it all the time if I could. I think that her refusal to participate has lead to my fantasies getting more and more bi. I used to fantasize about dressing for her and being pegged. Now I fantasize about fucking and sucking real cocks.